


A sweet disorder in the dress

by saltandbyrne



Category: Supernatural
Genre: Barebacking, Bottom Sam, Community: spn-masquerade, Corsetry, Crossdressing, Feminization, High School, M/M, Possessive Dean Winchester, Sibling Incest, Top Dean, Top Dean Winchester/Bottom Sam Winchester, Underage Sex, Weecest
Language: English
Status: Completed
Published: 2015-09-27
Updated: 2015-09-27
Packaged: 2018-04-23 15:51:22
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,525
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4882798
Author URL: https://archiveofourown.org/users/saltandbyrne/pseuds/saltandbyrne
Summary: <blockquote class="userstuff">
              <p>Dean leans forward a little as the other actors start to speak.  Both of the ones in dresses try to pitch their voices up but there’s no mistaking it.  Everyone’s in drag, as far as he can tell.</p><p>Dean’s heart skips a little.</p>
            </blockquote>





	A sweet disorder in the dress

**Author's Note:**

> Written for round 3 of spn-masquerade for the prompt: Weecest where Sam gets a part in a Shakespeare play at his highschool and he's stuck in a girls role, and of course - of course - the parents are supposed to help with costumes and all that, basically, where I'm going with this is teen Sam in a brocade dress that Dean hates because jfc it takes forever to sew that shit, and they end up fucking in the dressing room after the play while Dean rips it off him. :D
> 
> Sam is in high school, age unspecified.

“What happened to your hand?”

 

Dean sets Sam’s spaghetti down on the table and points to the bandaid over Sam’s thumb.

 

“Nothing.”

 

Sam tucks his hand into the baggy sleeve of his sweatshirt. Nothing fits Sam these days, like he’s made out of half grownup parts and half kid parts.  Something’s always hanging over his knuckles or leaving his ankles bare to the nippy Oskaloosa fall. 

 

“Nothing?”

 

Dean arches an eyebrow as he twirls his fork into his dinner.  It’s hard not to put on the dad face when Dean’s been cooking dinner for the past two weeks.

 

“I stuck myself with a sewing needle, Dean. You happy?”

 

Dean snorts.  Dad’s been gone for two weeks, Sam gave him head this morning, and the only injury either of them has is from Sam’s foray into costuming. He’s been a hell of a lot worse.

 

“Least you’re up on your tetanus shots.”

 

Sam rolls his eyes and stuffs a forkful of pasta into his mouth.  God, Sam can eat these days.

 

“Can’t believe they’ve got you sewing britches or whatever the fuck you’re supposed to be wearing.”

 

“Breeches,” Sam mumbles around his food.

 

“Sounds like free labor to me.”

 

Dean bites into a meatball.  They’d been on sale at the Fareway and Dean had stocked up, flush enough for once to pack their rental freezer. 

 

“I don’t mind.”

 

Sam shrugs.  He’d been clammy about this damn play ever since he’d been picked for a role.

 

“When’s your big night on stage, anyway?”

 

“Uh, Thursday.”  Sam stacks two meatballs on his fork and shoves them both in his mouth like Dean never taught him any manners.

 

“I’ll see if I can get off work.”

 

Dean’s been trading shifts busing tables at a mediocre diner and filling in at a damn good auto body shop.

 

“Whatever, you don’t have to.” Sam nudges another meatball across his plate, smearing it through red sauce.

 

Dean narrows his eyes at the way Sam is adamantly not looking at him.  He’s hiding something. 

 

“You been staying late every night to help with this thing, Sammy, of course I wanna see.”

 

Sam’s face gets a little redder as he darts a glance up at Dean.  Dean smiles, sliding his foot under the table until his threadbare sock hits Sam’s bare ankle. Dean’d find him out in due time, he always does.

 

“You finish your homework?”

 

Dean trails the side of his foot against Sam’s skin as he pushes his plate aside.

 

“Yeah.”

 

Sam’s bangs fall in his face as he nods, looking up at Dean and biting his lip.

 

“Good.”

 

Dean reaches out to rub his thumb over Sam’s bandaid.

 

“Cause I wanna kiss this all better.”

 

~

 

Dean does not miss high school. Maybe the cheerleaders, sometimes, but not that oppressive green paint and that grid caging they all have over the windows.  Dean’s been booked for some small shit and he knows a cell when he sees one.

 

At least the auditorium seats are mostly padded.

 

Dean folds his Xeroxed program and tucks it inside his jacket.  Schools like this still shut off the heat after six and Dean’s glad for the extra layer of his flannel shirt under his leather jacket.

 

The lights dim and Dean spreads his arm across the empty seat next to him.  It’s worth being bored to tears to make Sam happy, but at least he can be sort of comfortable.

 

He knows Sam doesn’t have one of the lead roles, but from what he could wheedle out of Sam he knows he has some decent time on stage. 

 

Dean’s sitting in the back so he has to squint a little as the first couple of kids take the stage.  He can hear Sam correcting him – _actors, Dean_.  The actors on stage wait for the applause to subside and barrel right into their lines. Dean smiles at the guy in the bloomers or brinches or whatever they’re called.  His voice is really high.  Too high, actually.

 

That’s not a guy.

 

Dean leans forward a little as the other actors start to speak.  Both of the ones in dresses try to pitch their voices up but there’s no mistaking it. Everyone’s in drag, as far as he can tell.

 

Dean’s heart skips a little.

 

It’s twenty minutes before Sam takes the stage, not that Dean recognizes him at first.  He’s got a blond wig on and a dress that trails on the floor behind him as he sweeps across the stage.  When he opens his mouth to speak Dean presses a hand over his mouth.

 

Sam is fucking gorgeous.

 

He’s wearing a ton of makeup. His eyes look enormous and he’s get enough blush on his cheeks to make him look like he just got fucked within an inch of his life.  It’s a look Dean knows well and holds close to himself, one of those flushed secrets he’ll guard until he dies.  His lips are bright, pulsing pink, pouted into a cute smile as Sam banters with one of the other actors.

 

Dean has never wanted to put his dick in Sam’s mouth so bad in his life.

 

The auditorium has warmed up a little between the stage lights and the audience of cooing parents, and thank God. Dean’s pretty adept at hiding awkward boners in school and having a jacket in his lap is pretty much the only thing keeping him from being in flagrant violation of several decency laws right now.

 

Sam stumbles over a few of his lines, but he makes up for it with the graceful, distracting way he moves around the stage like he owns it.  His dress looks like something a slutty girl at a ren faire would claw her best friend’s eyes out for, nipped into Sam’s slim, tiny waist and Christ, is he wearing some kind of corset?

 

Dean risks a hand under his jacket, pressing against his dick for a brutal second.

 

He watches Sam stand in profile, watches the rise and fall of his chest.  He’s got something stuffed in his dress that makes it look like he even has little tits.

 

Sam has the prettiest nipples.

 

Whatever dead white guy wrote this play clearly never heard of editing.  Dean’s squirming in his seat a half-hour before the damn thing ends, hard in his jeans and glad he has the row to himself. 

 

He bites his cheek and wills his dick into reluctant obedience. At least the last few scenes don’t have Sam in them.

 

He’s back to whatever passes for his normal by the time the curtain falls.  Sam and the rest of the cast come out for their final bow and Dean stands up tall, applauding and smiling that smile that always got the cheerleaders out of their skirts.

 

Sam stumbles a little when he catches Dean’s eye.

 

Dean ignores the polite conversational attempt of a clutch of mothers as he hovers by the stage.  Just thinking of Sam hugging his castmates and walking around in that goddamn dress makes his blood run hot, that same ribbon of jealousy that tightens around him whenever Sam gets settled into a new place.

 

Sam’s not supposed to be pretty for anyone but him.

 

His blush is masked by all that makeup when Sam finally comes out the side door with the rest of the actors, but Dean can read him, always can. 

 

“Didn’t think you’d come.”

 

Dean swallows, his fists clenched by his sides so he won’t get anything more than proud big brother close to Sam.

 

“You gonna take me backstage and gimme your autograph, Samantha?”

 

“You’re not, um, you’re not mad?”

 

Dean’s back is turned to everyone else, so no one can see when he palms himself, just long enough to make Sam’s eyes widen under what must be fake eyelashes.  They never flirt in public, never so much as kiss on the cheek when they both know what’s at stake but Dean doesn’t give a fuck right now, not when Sam’s lips are parting wide and painted pink.  They won’t be here much longer anyway.

 

“Gonna be if I don’t get you alone real quick, Sam.”

 

He says it just loud enough that someone could overhear.  Sam opens and closes his mouth a few times before he manages to move.

 

Dean follows him through a rabbit warren of hallways, and even that horrible fluorescent lighting can’t ruin how gorgeous Sam looks every time he glances back to make sure Dean’s still behind him. Like Dean would be anywhere else.

 

Sam leads them to a cramped room with a bare bulb and an impromptu dressing table set on saw horses.  A mirror leans against the wall, gilt painting flaking off the prop frame.  Dean kicks the door shut behind them.

 

“Please tell me this locks.”

 

He doesn’t wait for an answer before he backs Sam up against the door and kisses him.  Sam fumbles for the flimsy hook and eye lock nailed into the door. Dean’s kissed a lot of lipstick off a lot of people but it’s never made him this hard.

 

“Jesus Christ, Sammy.”

 

Dean doesn’t know where to touch first. Sam’s wig slips off in his hands and he tosses it aside, running his hands through Sam’s sweaty hair until it stands up messy for him.

 

“Why didn’t you tell me?”

 

Sam huffs against him, his hand clutching into Dean’s shirt.

 

“I dunno, I thought you’d, like, think it was stupid or something.”

 

Sam sounds so young and that shouldn’t make Dean’s dick jerk like that.

 

“M’gonna fuck you stupid,” Dean mumbles, his mouth occupied with a soft swathe of Sam’s throat.  Sam’s heart always beats so fast against his lips.

 

They stumble back, Sam’s slippers or whatever the fuck they are tangling in Dean’s boots.  There’s crap everywhere.  A giant Styrofoam palm tree thuds on its side as Sam knocks against it and Dean kicks a particle board dairy cow against the wall.

 

Dean hits the table and grabs Sam by the waist, his mouth falling open.

 

“Tell me there’s lingerie under that,” Dean licks into Sam’s ear, letting his hands roam over some kind of boning that’s holding Sam’s waist in so tiny Dean can almost get his fingers to touch.

 

“They’re, unh, they’re called stays.”

 

Dean snorts as he spins Sam around. Sam’s forearms hit the table, knocking over a haphazard stack of small jars and pots of oily looking shit.

 

“Well they’re staying on,” Dean jokes, his dick still aching hard but his heart softening a little at Sam’s eye roll.

 

Sam’s eyes roll again, a different kind of taken aback when Dean hikes his skirt up, bunching thick fabric in his hands until he can flip it over Sam’s waist.

 

“Jesus, Sammy.”

 

Sam’s got stockings on.

 

They only come to his knees, elastic cinching them tight around Sam’s bony legs.  Sam’s thighs trail up, shifting with that nervous kickback Sam always gets when Dean throws him around.

 

Sam’s still got his own underwear on, his briefs looking out of place under the laced back of his corset, Dean knows a goddamn corset when he sees one.  He pushes Sam’s dress up far enough to clasp his hands around Sam’s waist, squeezing.

 

“Your little friends see you all dressed up like this, Sammy?”

 

He hikes Sam back, smiling at the way Sam’s ass automatically sticks up in the air as his legs spread.  Sam can look as cute as he wants for the drama club.

 

“Not, not like this, Dean, never.” Sam looks in the mirror, catching Dean’s eye and shaking his head, like Dean would doubt him. Sam only gives it up like this for Dean, that’s one of the only things Dean knows for sure in life.

 

He folds himself over Sam, letting his cock press hard against Sam’s ass as he kisses up the graceful curve of Sam’s neck. He smells like powder and that weird not-a-scent all makeup seems to have. 

 

“Didn’t know you could be so fucking pretty, Sammy.”

 

Sam closes his eyes as Dean grips his jaw, just firm enough to push Sam’s lips into an open pout.  Dean’s buying him more lipstick tomorrow.

 

He flattens his hand on Sam’s back, his palm bleeding heat into Sam’s corset lacing as he rears back up.  He tugs Sam’s briefs down just to watch Sam grimace as his dick hits the table.  Sam’s hard for him.

 

“Such a goddamn tease, Sammy.”

 

Dean spit-slicks a finger and circles it around Sam’s hole, pushing in before Sam can get an answer out.

 

“Swinging that ass around all pretty, Christ.”

 

Dean groans as Sam swallows two of his fingers, wincing a little because spit isn’t good lube and they both know it. Sam doesn’t seem to care too much as he fucks himself back onto Dean’s hand.

 

“Dean,” Sam moans, balling his hands into fists on the table.  Dean glances at the beauty supplies littering the table, smiling greedy when he seems a familiar blue-topped jar. Thank God.

 

He grabs the Vaseline and grins at Sam in the mirror.

 

“Got so fucking hard watching you, baby.”

 

Dean’s growl stays in his chest as he unzips himself. His cock jerks in his hand, impatient and Dean can’t blame it.  Sam looks sin-pretty spread out like this, briefs bunched around his thighs and that pretty painted face staring back at him in the mirror.

 

“Dean, wait.”

 

Dean sucks his fingers wet just because he can before he pushes them back into Sam.   It’s been a good couple of weeks and Sam opens easy for him, muscle giving way as Dean fucks him knuckle-deep.

 

Sam’s getting used to taking it every day.

 

“You ready for me?”

 

“Yeah, I’m, yeah, it’s just,” Sam huffs, pushing himself up.

 

“Do you have a condom?”

 

Dean’s eyebrows go up a few good inches. Sam always takes him bare, always.

 

“What’s the matter, sweetheart?”

 

Dean cocks a grin.

 

“Afraid I’m gonna knock you up?”

 

He twists his fingers inside Sam, hitting that spot where Sam’s eyes flutter closed and his eyes roll back. God that looks even better with all that eye makeup on.

 

“We just, fuck, we shouldn’t ruin the dress.”

 

“Oh, Sammy.” Dean clicks his tongue as he scoops two fingers into the Vaseline.

 

“I’m gonna buy you lots of pretty dresses, don’t you worry.”

 

He slicks himself up and wipes the rest around Sam’s hole, pushing it in with his thumb. 

 

“Get you lots of pretty things to wear for me.”

 

This used to be the scary part, this first push into Sam where he seems too small to ever take Dean’s cock, where they can’t possibly fit together. 

 

Dean doesn’t even watch as he sinks in now, just grabs Sam under the chin so he can watch his face reflecting back as he flexes open for Dean.  Sam looks pretty in his makeup and his fancy dress and his laced-in little waist, but Sam looks perfect when he’s taking Dean’s cock to the base and panting like he’s thirsty for more.

 

“Like being a pretty girl for me, Sammy?”

 

Dean bottoms out, grinding them both forward as Sam moans, open-mouthed. Dean doesn’t need to touch Sam’s dick to know he’s leaking precome. Sam’s gonna ruin that dress before Dean even pulls out of him.

 

“Gets you wet hiking your little skirt up for me.”

 

Dean gets a grip on Sam’s dick, stroking up and groaning as his thumb smears wet.  He uses his thrusts to fuck Sam up into his hand, working up until he’s shaking the saw horses holding them up.  Sam’s eyes never leave him, going glassy as he braces himself and flutters his eyelashes, so fucking pretty.

 

“Need your big brother to fuck your little pussy till you come, don’t you, Sammy?”

 

Dean tucks down against him, curling his back so he can get his mouth on Sam’s neck.  He buries his cock deep and jerks him quick, pulling a little rough on the upstroke the way Sam likes. 

 

“Yeah, Dean, fuck,” Sam mumbles, scrabbling against the table as another pot of something sparkly clatters to the floor. Even under all that makeup Dean knows Sam’s face when he’s getting close, that strain on his neck, the way his eyes drift in and out of focus.  Christ, Dean would keep him like this all the time if he could, pull him out of school and lock them both up someplace where Dad could never find them and Sam could look this happy all the time.

 

Sam clenches hot when he comes, daring Dean to trip right after him.  Dean’s head swims, fuzzy and warm and willing himself to hold off so this never ends. He heaves for breath against Sam’s shaking back.

 

“Gonna make me come too soon, baby,” Dean kisses along his neck, along the sweaty collar of his dress, fabric ruined and dirty just like them.

 

“Take it so fucking good, Sam.”

 

Sam’s boneless as Dean hauls him up, barely holding him weight on his hands as Dean paws over his chest. Every shift of Sam’s body drives him deeper on Dean’s cock, ooze-tight heat of Sam’s hole just letting him in, made for it. Dean slips a hand under Sam’s neckline, dragging sweaty past his collarbone until he finds one of Sam’s nipples underneath soft padding.

 

“Want to see those pretty tits while I fuck you.”

 

Sam gasps when Dean grabs the lacy edge of Sam’s dress and tugs, ripping it open across the front.  Foam spills out, fake tits batted aside as Dean cups over Sam’s pec, squeezing hard to get a handful. 

 

Sam’s always had sensitive nipples.

 

Dean gets both hands on his chest, hard enough to bruise as Sam arches back, head knocking against Dean’s shoulder. Dean pinches at his nipples, grunting nasty at the pitiful sounds Sam makes as he tugs. 

 

“That’s my good girl, take that cock, come on.”

 

He fucks Sam hard, pulling him back to slap against Dean’s hips.  Sam moans filthy as they smack into each other, all wet sounds and labored breath and the Vaseline suck of Sam’s asshole when Dean pounds into him. 

 

Dean’s not gonna last.

 

There’s all kinds of shit Dean wants to say, about keeping Sam dressed up pretty for him all the time, fucking those lipstick lips until they’re smeared all over Dean’s cock, lacing Sam up tight until he can barely breathe when Dean fucks him, tucking Sam away someplace soft and secret like a jewel box ballerina just for Dean.

 

Dean chokes out Sam’s name when he comes and that’s good enough.

 

The table groans under their weight as Dean collapses on top of Sam, each breath shaky as his hands twine into Sam’s hair and he mumbles God only knows what against his ear.  His heart is still pounding in his throat when he rears back up, looking down.

 

He didn’t watch himself sink into Sam but he’s sure as shit gonna watch himself pull out.

 

If Dean could do one thing for the rest of his life it’d be coming in Sam’s ass, hands down, but even that isn’t as good as the wet slip when he pulls out.  Sam’s hole gapes slick-puffed and clenching, closing back up but not before a fat trail of Dean’s come seeps out to snake down his balls.  Dean watches it drip all the way to the floor before he pulls Sam’s briefs back up. 

 

Sam staggers to his feet.  His makeup’s smeared where his face had been pressed against the table, still pretty but not perfect and he’s just right for Dean to kiss.

 

He helps Sam change out of his ruined dress, feeling a surge of something hot and fucked up when Sam pulls his jeans on right over his come-soaked briefs.  Dean’ll never say it but this is what Sam should smell like all the time, fucked and full and Dean’s no matter what other part he’s playing.

 

Sam wipes off his makeup, looking like a kid again when he’s done, cheeks rosy fucked and his eyes puffy. 

 

“I can, you know, I can hang around if you wanna be with your friends, drive you home later.”

 

Dean shrugs, hating the offer but knowing Sam needs it, maybe.

 

Sam’s arms wrap around his neck, all that boy smell wafting up to Dean’s nose and making him go tight inside. Sam kisses him, slow and soft, like they’re not locked in a glorified closet and risking arrest just to have this.

 

“I want you to take me home so we can do that again.”

 

Dean smiles, all that ugly shit abating in him as Sam looks up at him.

 

He untucks himself from Dean and glances at the table, eyes narrowing.  He snatches up a slim tube of lipstick and tucks it in his pocket, blushing and squirming a little under Dean’s heavy gaze.

 

“I don’t think they’ll notice this missing,” Sam says, soft and unsure until Dean tugs him closer.  He unlocks the door and pulls Sam in for one last kiss.

 

“Nothing’s missing, Sammy.”

 

Sam leads him out of the school with neither of them looking back.


End file.
